ロイコトリエンA4
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/04/21 17:06:37」(JST)
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Leukotriene A4
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Names |
IUPAC name
4-{(2S,3S)-3-[(1E,3E,5Z,8Z)-1,3,5,8-Tetradecatetraen-1-yl]-2-oxiranyl}butanoic acid
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Systematic IUPAC name
4-{(2S,3S)-3-[(1E,3E,5Z,8Z)-1,3,5,8-Tetradecatetraen-1-yl]-2-oxiranyl}butanoic acid
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Identifiers |
CAS Registry Number
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72059-45-1 Y |
ChEBI |
CHEBI:15651 N |
ChemSpider |
4444074 N |
InChI
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InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1 N
Key: UFPQIRYSPUYQHK-WAQVJNLQSA-N N
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InChI=1/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1
Key: UFPQIRYSPUYQHK-WAQVJNLQBZ
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Jmol-3D images |
Image |
KEGG |
C00909 N |
MeSH |
D017572 |
PubChem |
5280383 |
SMILES
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CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)O
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Properties |
Chemical formula
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C20H30O3 |
Molar mass |
318.450 |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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N verify (what is: Y/N?) |
Infobox references |
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Leukotriene A4 is a leukotriene.
Leukotriene A4 hydrolase converts it to Leukotriene B4. Leukotriene C4 synthase converts it to Leukotriene C4.
Eicosanoid synthesis. (Leukotrienes at right.)
Autacoids, unsaturated fatty acids: Eicosanoids
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Precursor |
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Prostanoids |
Prostaglandins (PG) and
analogues |
Precursor |
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Active |
D/J |
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E/F |
- E2 (Dinoprostone): Enprostil
- Sulprostone
- E1 (Alprostadil): Misoprostol
- Gemeprost
- F2α (Dinoprost): Bimatoprost
- Carboprost
- Latanoprost
- Tafluprost
- Travoprost
- Unoprostone
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I |
- I2 (Prostacyclin/Epoprostenol): Beraprost
- Iloprost
- Treprostinil
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Thromboxanes (TX) |
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Leukotrienes (LT) |
Precursor |
- Arachidonic acid 5-hydroperoxide
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Initial |
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SRS-A |
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Eoxins (EX) |
Precursor |
- Arachidonic acid 15-hydroperoxide
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Eoxins |
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Nonclassic |
- Lipoxins (A4, B4)
- Virodhamine
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By function |
- vasoconstriction
- vasodilation
- platelets: induce
- inhibit
- leukocytes: induce
- inhibit
- labor stimulation:
- PGE2 (Dinoprostone)
- PGF2α (Dinoprost)
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Index of inborn errors of metabolism
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Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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Treatment |
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
- Tetrapyrroles
- intermediates
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UpToDate Contents
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English Journal
- The arachidonic acid-LTB4-BLT2 pathway enhances human B-CLL aggressiveness.
- Guriec N1, Le Jossic-Corcos C2, Simon B2, Ianotto JC3, Tempescul A3, Dréano Y2, Salaün JP2, Berthou C4, Corcos L2.
- Biochimica et biophysica acta.Biochim Biophys Acta.2014 Nov;1842(11):2096-105. doi: 10.1016/j.bbadis.2014.07.016. Epub 2014 Jul 26.
- Deregulation of the oxidative cascade of poly-unsaturated fatty acids (PUFAs) has been associated with several cancers, including chronic lymphocytic leukemia (B-CLL). Leukotriene B4 (LTB4), a metabolite of arachidonic acid (AA), is produced by B-CLL and contributes to their survival. The aim of the
- PMID 25072959
- Resolvin D1 limits 5-lipoxygenase nuclear localization and leukotriene B4 synthesis by inhibiting a calcium-activated kinase pathway.
- Fredman G1, Ozcan L2, Spolitu S2, Hellmann J3, Spite M3, Backs J4, Tabas I1.
- Proceedings of the National Academy of Sciences of the United States of America.Proc Natl Acad Sci U S A.2014 Oct 7;111(40):14530-5. doi: 10.1073/pnas.1410851111. Epub 2014 Sep 22.
- Imbalances between proinflammatory and proresolving mediators can lead to chronic inflammatory diseases. The balance of arachidonic acid-derived mediators in leukocytes is thought to be achieved through intracellular localization of 5-lipoxygenase (5-LOX): nuclear 5-LOX favors the biosynthesis of pr
- PMID 25246560
- Pro- and anti-inflammatory mediators change leukotriene B4 and leukotriene C4 synthesis and secretion in an inflamed porcine endometrium.
- Czarzasta J1, Andronowska A1, Jana B2.
- Domestic animal endocrinology.Domest Anim Endocrinol.2014 Oct;49:49-59. doi: 10.1016/j.domaniend.2014.05.001. Epub 2014 May 21.
- We studied the effect of lipopolysaccharide (LPS), proinflammatory cytokines (tumor necrosis factor α [TNF-α] and interleukin [IL]-1β), and anti-inflammatory cytokines (IL-4 and IL-10) on leukotriene (LT) A4 hydrolase and LTC4 synthase (LTCS) protein expression in, and LTB4 and LTC4 secretion fro
- PMID 25010026
Japanese Journal
- Purification and Characterization of Porcine Skeletal Muscle Aminopeptidase T, a Novel Metallopeptidase Homologous to Leukotriene A_4 Hydrolase
- Sarker Mohammed Alamgir,Matsuda Shinji,Mizutani Osamu [他],RAO Shengbin,MIGITA Koshiro,GOTO YAMAMOTO Nami,IEFUJI Haruyuki,NISHIMURA Toshihide
- Bioscience, biotechnology, and biochemistry 75(6), 1154-1159, 2011-06-23
- A novel aminopeptidase, Aminopeptidase T (APase T), was purified from porcine skeletal muscle following successive column chromatography: twice on DEAE-cellulose, hydroxyapatite, and Sephacryl S-200 H …
- NAID 10029328354
- Leukotrienes in Nociceptive Pathway and Neuropathic/Inflammatory Pain
- Noguchi Koichi,Okubo Masamichi
- Biological and Pharmaceutical Bulletin 34(8), 1163-1169, 2011
- … We found the expression of 5-lipoxygenase (5-LO), FLAP and the cysteinyl leukotrienes (CysLT1) mRNAs in spinal microglia, LTA4h and LTC4s mRNAs in both spinal neurons and microglia, and BLT1 mRNA in spinal neurons. …
- NAID 130000936581
- Role of Leukotriene B4 in 5-Lipoxygenase Metabolite- and Allergy-Induced Itch-Associated Responses in Mice
- Tsuji Fumio,Aono Hiroyuki,Tsuboi Takashi [他],Murakami Tadahiro,Enomoto Hiroshi,Mizutani Keiko,Inagaki Naoki
- Biological and Pharmaceutical Bulletin 33(6), 1050-1053, 2010
- … We investigated the role of leukotriene (LT) B4 in 5-lipoxygenase metabolite- and allergy-induced itch-associated responses using SA6541, an LTA4 hydrolase inhibitor. … By screening molecules related to arachidonic acid metabolism or pruritus, SA6541 was found to be a specific inhibiter of LTA4 hydrolase. …
- NAID 130000247978
Related Links
- 納期について TANOSEE レタートレー A4タテ クリア TM-LTA4-C の発送目安は、次の通りです。 代引き:今すぐ注文確定で 2015/10/14発送 振込等:今すぐ注文-入金確認で 2015/10/14発送 ※目安であり確約納期ではございません。 ...
- Buy LTA4 (Leukotriene A4 methyl ester) (CAS 73466-12-3), an unstable intermediate in the biosynthesis of LTB4 and LTC4, from Santa Cruz. Purity: ≥95% ... LTA4 (Leukotriene A4 methyl ester) is a member of the leukotriene family ...
Related Pictures
★リンクテーブル★
[★]
- 英
- leukotriene, LT
- 関
- アラキドン酸、5-リポキシゲナーゼ
合成
- 白血球遊走
- 気管支平滑筋収縮、細動脈収縮、血管透過性亢進
構造
種類
[★]
ロイコトリエンA4
- 関
- leukotriene A、LTA4
[★]
- 英
- LTA4
- 関
- ロイコトリエン
[★]
[★]
life-threatening arrhythmia